Huang Wen-Jun, Ma Ya-Ya, Liu Li-Xia, Wu Bo, Jiang Guo-Fang, Zhou Yong-Gui
Advanced Catalytic Engineer Research Center of Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, PR China.
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, Liaoning 116023, PR China.
Org Lett. 2021 Apr 2;23(7):2393-2398. doi: 10.1021/acs.orglett.0c04002. Epub 2021 Mar 18.
The direct regio- and enantioselective C6 functionalization of 2,3-disubstituted indoles with azadienes has been developed using chiral phosphoric acid as catalyst, providing a convenient approach to synthesize the optically active heterotriarylmethanes with excellent yields, broad substrate scope, and up to 98% ee. Mechanistic studies revealed that -alkylation of 2,3-disubstituted indoles with azadienes would be reversible, and enantioselective C6 functionalization could be enabled.
以手性磷酸为催化剂，实现了2,3-二取代吲哚与氮杂二烯的直接区域和对映选择性C6官能化反应，为合成光学活性的杂三芳基甲烷提供了一种简便方法，该方法具有优异的产率、广泛的底物范围和高达98%的对映体过量值。机理研究表明，2,3-二取代吲哚与氮杂二烯的α-烷基化反应是可逆的，并且可以实现对映选择性C6官能化。
